Like many stretches of Midwestern highway, the northerly drive on Route 131 toward Traverse City is a banal, zoned-out-zombie experience. Frustrated travelers must log miles and miles of uninteresting flatland until, just past Cadillac—finally—trees! Car windows roll down in unison as drivers and their passengers inhale the tingling pine-scented breeze. This is Michigan.

Leelanau County is awash with charming off-the-beaten-path B & Bs, but Traverse City, which lies just beyond the county’s southeastern edge, offers the largest mix of lodging, from chain hotels to historic mansions. Make a reservation at Antiquities’ Wellington Inn, where Barb Rishel, the proprietor, dispenses an encyclopedic knowledge of the area while you chomp on her freshly baked cookies. The inn itself is a meticulously restored neo­classical manse built in 1905 for the lumber baron William Cary Hull. A few modern room features (whirl­pool tubs and free Wi-Fi) disturb the Edith Wharton fantasy a smidge, but it’s a small price to pay.

From there, take a short walk to Front Street, the hub of the downtown business district. Catch an indie film at the renovated State Theatre, operated year-round by the Traverse City Film Festival (founded by the Academy Award– winning director Michael Moore), watch the tall ships glide across Grand Traverse Bay, or grab dinner at one of the three area restaurants that were semifinalists for James Beard awards in 2010. One of them, Trattoria Stella, two miles southwest of the inn, is situated in The Village, a 63-acre reclamation project of Victorian Italianate buildings (originally the Northern Michigan Asylum for the Insane). The chef, Myles Anton, whips up delicious but unfussy Italian dishes using the freshest picks from more than a dozen regional farms, while Amanda Danielson, the sommelier, curates a thoughtful list of Italian and surprisingly pleasant local wines.

Because of the cooler climate, this is riesling territory. Sweet is the name of the game, and many area wineries also produce fruit wines (this is the cherry capital, after all) with flavors that, for some, might spark memories of college and a bad brush with Sunset Blush Franzia. You could create an entire itinerary of wine tours by driving (or biking) up and down the scenic Old Mission and Leelanau peninsulas, but there are only a handful of wineries that craft sophisticated bottles. Left Foot Charley, in the asylum’s former laundry facility, popped up twice as a server’s recommendation, and our glasses of Seventh Hill Farm 2008 riesling and Murmur, a 2009 house blend of pinot gris, riesling, and gewürz­traminer, didn’t have us reaching for the insulin.

To stave off high blood pressure, go west on Highway 72 for an outdoor workout at Sleeping Bear Dunes National Lakeshore. At the visitor’s center in Empire, pick up a map and a $10 pass (good for one car for a week), then head a few miles south to the Empire Bluff Trail. The one-and-a-half-mile hike twists through a canopy of colorful beech and maple trees and rewards walkers with an eye-popping view of Lake Michigan, masquerading as the Mediterranean. Those wanting to feel the burn can tramp up the infamous Dune Climb. The initial hill is manageable for most—locals like to spook you about the strain to the top—but it’s true that the longer hikes will zap your stamina. Many tourists ignore warnings and slide down a 450-foot drop from the Lake Michigan Overlook, one of the stops along the must-see Pierce Stocking Scenic Drive, then crawl back up. (Only do this if you want to repopulate the abandoned asylum.) Although little more than seven miles long, Pierce Stocking can fill half a day or more with its lake views, dune trails, and stellar samplings of fall’s lustrous transformation that beg you to pull over and have a picnic.

Weary from all that exertion? Claim your reward in Glen Arbor. It takes less than 15 minutes to walk the length of the town, which bustles with tourists making pit stops at the flagship location of Cherry Republic, a three-building compound brimming with every possible kind of cherry product. (If there’s a nip in the air, try a glass of spiced wine there.) Then book a 7 p.m. dinner reservation at Blu, another James Beard semi­finalist. Request a table next to its floor-to-ceiling windows, sip a crisp riesling, and relax as the waters of Lake Michigan turn from turquoise to fluorescent orange.

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For kid-friendly fun, make a detour to the Maritime Museum, near the historic village of Glen Haven. Don’t miss the boathouse, where volunteers give a detailed account of the ingenious apparatus used by crewmen of the U.S. Life-Saving Service from 1901 to 1942. Braver souls can re-create a beach patrol on October 10th and 17th. Visit nps.gov/slbe for hours and more information. The museum closes for the season on October 18th.